I actually think Tailscale may be an even bigger deal here than sysadmin help from Claude Code at al.
The biggest reason I had not to run a home server was security: I'm worried that I might fall behind on updates and end up compromised.
Tailscale dramatically reduces this risk, because I can so easily configure it so my own devices can talk to my home server from anywhere in the world without the risk of exposing any ports on it directly to the internet.
Being able to hit my home server directly from my iPhone via a tailnet no matter where in the world my iPhone might be is really cool.
I am not sure why people are so afraid of exposing ports. I have dozens of ports open on my server including SMTP, IMAP(S), HTTP(S), various game servers and don't see a problem with that. I can't rule out a vulnerability somewhere but services are containerized and/or run as separate UNIX users. It's the way the Internet is meant to work.
There was a popular post less than a month ago about this recently >>46305585
I agree maintaining wireguard is a good compromise. It may not be "the way the internet was intended to work" but it lets you keep something which feels very close without relying on a 3rd party or exposing everything directly. On top of that, it's really not any more work than Tailscale to maintain.
That's where wg/Tailscale come in - it's just a traditional IP network at that point. Also less to do to shut up bad login attempts from spam bots and such. I once forgot to configure the log settings on sshd and ended up with GBs of logs in a week.
The other big upside (outside of not having a 3rd party) in putting in the slightly more effort to do wg/ssh/other personal VPN is the latency+bandwidth to your home services will be better.
I would argue OpenVPN is easier. I currently run both (there are some networks I can’t use UDP on, and I haven’t bothered figuring out how to get wireguard to work with TCP), and the OpenVPN initial configuration was easier, as is adding clients (DHCP, pre-shared cert+username/password).
This isn’t to say wireguard is hard. But imo OpenVPN is still easier - and it works everywhere out of the box. (The exception is networks that only let you talk on 80 and 443, but you can solve that by hosting OpenVPN on 443, in my experience.)
This is all based on my experience with opnsense as the vpn host (+router/firewall/DNS/DHCP). Maybe it would be a different story if I was trying to run the VPN server on a machine behind my router, but I have no reason to do so - I get at least 500Mbps symmetrical through OpenVPN, and that’s just the fastest network I’ve tested a client on. And even if that is the limit, that’s good enough for me, I don’t need faster throughput on my VPN since I’m almost always going to be latency limited.